


The Underwear Gala

by chucks_prophet



Category: Supernatural
Genre: Blow Jobs, Brotherly Love, Busty Asian Beauties, Cos It's Me, Cute, Dean Winchester in Lust, Dean in Panties, Established Jessica Moore/Sam Winchester, Face-Fucking, First Meetings, Humor, M/M, Masturbation, Model Castiel, Panties, Porn, Porn Watching, Porn With Plot, Public Blow Jobs, Sam Winchester in Love, Semi-Public Sex, Sexual Humor, Smut, Some Fluff, Some Plot, Underwear, What else is new?
Language: English
Status: Completed
Published: 2018-05-27
Updated: 2018-05-29
Packaged: 2019-05-14 08:10:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,949
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14765825
Author URL: https://archiveofourown.org/users/chucks_prophet/pseuds/chucks_prophet
Summary: He doesn’t waste time clicking on the video.Except, instead of three attractive Asian women, Dean’s eyes are introduced to an attractive Caucasian male. It’s an ad for some up-and-coming underwear company made “by and for men who need extra support”.Dean has to disagree with the comment. The only support this guy needs is a strong pair of hands hoisting him up and around a similarly built waistline.





	1. The Underwear

**Author's Note:**

> I dunno where this came from, as with most ideas, but enjoy!!!!

It isn’t an exaggeration to say he has Dean by the balls on a Friday evening in his room.

Dean got the notification this morning in his Social (because the leading stars are _very_ sociable with the camera) about a new Beauty joining the cast, and has been waiting ever since to properly enjoy it. For Dean, this means stripping down to his pink lace panties and sinking into his desk chair.

Although he’s eager as a church mouse on Sunday, he takes his time adjusting himself, testing just how far he can spread himself before the fabric bar between his cheeks chokes them. Once he’s satisfied, he reaches for the lube on his nightstand and slathers a healthy portion in his hands, loving the way it glides against his calloused hands.

Reaching into his lace to grab his equally eager prick feels more like diving head-first into a pool on a warm summer’s day, but he basks in the jarring sensation. He begins to stroke once he embraces the double-glazed warmth his cock has to offer. They’re slow and soft, his ministrations. Only the quietest moans and sighs escape his punctured throat, like a balloon gradually losing its helium.

Needless to say, he doesn’t waste time clicking on the video.

Except, instead of three attractive Asian women, Dean’s eyes are introduced to an attractive Caucasian male. It’s an ad for some up-and-coming underwear company made “by and for men who need extra support”.

Dean has to disagree with the comment. The only support this guy needs is a strong pair of hands hoisting him up and around a similarly built waistline.

The man’s sitting on a stool against a white backdrop. There’s a narration going, but Dean can’t bother listening when the camera zooms in on the man’s tanned face. The lens probably only captures a kernel of the shine reflecting in his sapphire eyes, like a lighthouse casting on the surface of the night-tinted ocean. Not to mention his hair. The color is akin to espresso and the physical representation of someone _after_ a cup of the liquid fire—defeating the purpose of sex hair.

The frame pans lower, drawing Dean’s eyes to his lower lip, emphasized by the man’s tongue. They’re beautiful lips. Puffy, pink, and pointed like a pair of cat’s ears at both parallel lines making up his stubbled Cupid’s bow. Dean finds himself doing the same when they pan to the rest of his lightly bearded half, across his long neck and past his dancing Adam’s apple, and a chest you can ski on—though, Dean doubts anyone would gloss over those perky brown nipples and the divots underneath them.

He’s trim, but packing in the arms and thighs. Dean can’t accurately describe the shape of his crotch without rewinding. The man’s large hands smother the front of the white boxer briefs the first chance he gets before it fades out to a whiter overlay with the company’s name and contact information.

“ _Dean!_ Our Uber’s picking us up in 10!”

“Won’t take me that long,” Dean mumbles.

Sure enough, even his pain-in-the-ass little brother can ruin the mood this time. He bucks up into his hand after just a few strokes. A second less passionate moan escapes him as he realizes just what he’s wiping himself with: the black pullover to his Ralph Lauren three-piece he bought _just_ for the gala.

He laughs to himself almost immediately after he straightens it out in front of him to survey the damage: “Lady Gaga would pay ten grand for this.”

 

 

“What’re you whistling to yourself about over there?”

Dean glances up from his phone. “Hmm? Oh ha-uhm, nothing. Just catching up with the Kardashians.”

“Dean, I swear to God, if you’re browsing porn on a _first-class flight.”_

Dean regrets not responding to Sam’s accusation after he snatches the phone from his hands. “Hey! That’s not very _first-class_ behavior,” he shoots back, though can’t find it in him to complain too much when he sinks into a massage-capable leather chair every few seconds.

His panic rises again when Sam chuckles, “Oh my God. You’re browsing the guest list for the gala!?”

“So?”

“What happened to being completely disinterested in the fashion universe?”

“I’m not looking at _Vera Wang,”_ Dean protests, stealing his phone back, “I’m looking at Vera _Farmiga.”_

Sam scoffs, “You really believe you’re gonna have sex with one of the stars?”

“Correction: I _know_ I’m gonna have sex with one of them,” he says. He starts to cut his filet mignon before emphasizing with his fork at Sam. “And I can also guarantee their five-thousand dollar gowns’ll look way better on the floor of our hotel room.”

Sam drops his head, hair dropping along with him. “Please don’t say that sort of stuff around Jess, okay? She worked really hard to get her stuff in the show. And it’s really good.”

Dean pauses to look at his brother. His hair’s actually well-tamed, considering it nearly touches his shoulders. He hasn’t worn a brand-name button-down since senior prom. It’s a nice compliment to his chocolate stubble. He’s really serious about Jess, and it shows in more than just the way he dresses. He’s got his glow back—something Bela nearly stole from him a few years prior.

Dean wants to reach out and clasp him on the shoulder, but knowing well enough Sam will make a big deal of Dean showing “affection”, he just contains his smile to a small lift of his lips and nods. “You got it, pal.”

Sam throws his head back. “ _Pal?_ What happened to bitch?”

“Jess is making one out of you as it is, so it would be redundant.”

Dean laughs when Sam throws his napkin at him, despite people around them staring. “Jerk,” Sam curses without heat.

They resume eating, Dean continuing to read the extensive list of celebrities. One name catches his eye, just from the uniqueness: Castiel Novak. Dean doesn’t bother with it, though. It’s probably just another budding popstar with a penchant for picking the most outlandish name possible.

That, and Jessica Alba’s name is right above it.

Jess mentioned designing her dress, and he has to admit, Sam’s girlfriend is kind of his hero. Who else is gonna make these A-list celebrities look drool-worthy?

He falls asleep a few hours later dreaming of the gala.


	2. The Gala

**Summary for the Chapter:**

> Dean gulps. Judging by the wicked smirk crossing Cas’s face, he knows. “Do you work for the NSA on the side?” he jokes, though he’s kind of fearful of his answer with Cas stepping closer.
> 
> Seeing those blue eyes frost over a camera is much different than being under their direct scrutiny. Too bad he’s frozen in place; Dean feels like he has to take a step back just to thaw out. 
> 
> “No,” Cas answers, putting out his bottom lip with his tongue like a burning cigarette into an ashtray. He’s close enough now to touch Dean, but that would be too easy. “Otherwise, I wouldn’t ask you what you were wearing.”

Dean hasn’t seen so many flashing lights since the night of Sam’s senior prom, nor so many people around him. It’s the only time Dean can remember so many people gathered in one place—all to watch Sam stand by the front door: their mom, dad, Grandpa Henry, Aunt Ellen, Uncle Bobby, his fiancée Jody, her friend Donna, _her_ ex Doug, and _his_ new girlfriend. It was like they were visiting the local zoo to see Sam, the gangly little penguin, flop around in different poses, and get sunburnt glancing over at Amy Pond.

The gala is like that, just with a lot more wine and the guests are well-known across the _country,_ rather than the neighborhood.

“Jess designed _Charlize Theron’s_ dress?!” Dean howls before giving Sam a much-deserved, highly-refrained clasp on the shoulder. “Sammy, your girlfriend is awesome.”

“Speaking of the goddess herself,” Sam announces as Jess approaches them, sliding effortlessly into Sam.

Dean waits until Sam finishes swooning over his long-distance girlfriend—a moment that never actually comes to pass; it’s like Sam’s penny-colored eyes are trying to buy Jess’s diamond almonds—to greet Jess. He leans in and kisses her cheek, careful not to mess up her makeup. That’s probably a whole other art. “You look gorgeous, Jessica.”

After a moment, which is likely to blame on the undeniable stains across his suit, Jess smiles, stretching her cherry red lipstick. She really does look good. Like way-out-of-Sam’s-league good in a white V-neck dress and heels with lots of laces. It’s a good decision on her part to put up her blonde curls, because Sam’s hair’s quite the competition. “Thank you, Dean. And you look… like you’re not wearing flannel.”

“That good, huh? Don’t worry; I packed some just for you.”

“Oh good, for a second, I thought you and the nineties broke up.”

Dean’s airways clog before he can rejoin with something far wittier. A man in a silver tuxedo approaches her, copying Dean’s actions. Except, it’s not just any man: It’s the guy from the softcore underwear porn ad. He looks almost unrecognizable with clothes. “Jessica,” he greets with a voice deep and raspy enough to cause an earthquake in the LA area, “you’re looking exquisite, as usual.”

“Castiel,” she mock-scolds. “I see my suit’s holding up well.”

Dean’s eyes blow wide. Castiel, as in Castiel Novak, that weird name he saw on the list of attendees.

“That it is,” the man, Castiel, responds, glancing down at his tux. Dean doesn’t see the imprint of black angel wings on the lapels until Cas’s hands drop at his sides. It’s subtle, but classy—and fitting, considering the man’s angelic looks. Although, his combed back hair and freshly shaven face doesn’t make him look any less infernal. “You did a fantastic job: Again, as usual. And who do I have the pleasure of meeting?” he asks, glancing between Sam and Dean. Dean’s heart speeds up, leaving Dean racing to catch his breath.

“Cas, this is my boyfriend, Sam,” Jess introduces. The two shake hands and exchange niceties. “And this is his brother, Dean.”

Dean nearly forgets how to shake when Cas lends out his hand, which is irrefutably soft. It’s also the hand Dean got off to watching him grip his dick with, but those details can be left unspoken. “N-nice to meet you.”

Cas ogles him for a moment, and Dean checks himself. He’s not still shaking Cas’s hand and his eyes aren’t traveling south no matter how tempted he is, so he hasn’t done anything to prompt it.

Then a smile slides across Cas’s face like running water through the underside of a neighborhood sidewalk, just enough to tease Dean with a little bit of teeth: “Like James Dean.”

Dean shakes his head of every stupid thing he wants to blurt, even though it doesn’t seem to work when what comes out is: “Minus the exhibitionism. I don’t think I could whip it out just anywhere. Although, I do have to use the restroom. Excuse me.”

“As do I,” Cas states, to Dean’s surprise. “Excuse us.”

Dean keeps his head down as they maneuver backstage towards the bathrooms, only glancing over every so often to look at Cas. It’s a harder feat when they’re in the restroom, peeing next to each other. _Look at someone your own size,_ Dean silently reprimands, because _holy shit, he’s not even chubbed up._

“It must be surreal,” Cas says, interrupting Dean’s precise line of thought.

“Hmm?” Dean blurts ever-so eloquently.

Cas laughs as he zips up. “Being here, in LA. At a gala. You’ve been squirming in your suit every few seconds in just the past five minutes I’ve known you.”

Dean smiles and eases up on his white-knuckled grip on himself before shaking off. “Am I that obvious?”

“How big’s the city you live in?”

“Roughly ninety-five thousand. Lawrence, Kansas. What about you?”

“Impressive. Eleven thousand. Pontiac, Illinois.”

“Wow, that’s a long ways from home. What made you leave?”

“It’s kind of hard to model underwear under your parents’ roof.”

Dean gulps. Judging by the wicked smirk crossing Cas’s face, he knows. “Do you work for the NSA on the side?” he jokes, though he’s kind of fearful of his answer with Cas stepping closer.

Seeing those blue eyes frost over a camera is much different than being under their direct scrutiny. Too bad he’s frozen in place; Dean feels like he has to take a step back just to thaw out.

“No,” Cas answers, putting out his bottom lip with his tongue like a burning cigarette into an ashtray. He’s close enough now to touch Dean, but that would be too easy. “Otherwise, I wouldn’t ask you what you were wearing.”

“Uh-ha… um, lace pant-panties.”

“Anything else?”

“A hard dick,” Dean manages to grit through clenched teeth. Cas laughs. Just that puff of breath against his neck has his lower half twitching in interest.

“What color?”

“Pink.”

“Hmm,” Cas hums. “To match your cheeks and… other parts of you, I presume.”

Dean makes the fatal mistake of unleashing a laugh.

“What’s so funny?”

Dean clears his throat before letting his eyes flick to the growing tent in Cas’s own slacks, “Nothing, it’s just… imagining you in your underwear isn’t helping me this time around.”

“Why be limited to your imagination?”

Dean’s lips part a little, giving Cas invitation to kiss him. It’s chaste, nothing more than Cas’s lips closing around his, but it sets Dean’s chest aflame. Only when Cas pulls back does Dean realize the _lack_ of him equates to gasoline on flames, so he seals his scorching fate pulling Cas back into him.

Dean moans into his slick, wet heat, drawing patterns in Cas’s mouth with his tongue, when he hears people approaching.

Cas pulls back quickly, only to yank Dean by his tie and shove them into the nearest stall.

They kiss for a long time, tasting and feeling and learning—like Lewis and Clark after a two-year long expedition, and never having explored the maps of each other’s lips.

Cas’s hands cradle his face like he’s the original Fabergé egg. Dean’s a little less gentle. Let’s just say if Cas had real wings woven into his skin, Cas’s back would be shedding like a pillow after a gnarly pillow fight.

Cas must sense, _and feel,_ his growing impatience, because he pulls back and starts to strip. Except, with the departure of Cas’s lips, Dean’s left even more frustrated. “What’s… why—? _Oooh._ ”

Cas, the fucker, grins when his belt clatters on the tile. His slacks hang a little lower on his waist, exposing a thin stretch of bronze horizon. His mother taught him to never look directly into the sun, but it’s hard not to when Cas hooks his thumb in the front of his pants and tugs, teasing the arch of pubic hair surrounding his naughty bits.

“ _Fuck,_ Cas,” Dean grunts. “You’ve been commando this whole time?”

“Underwear is too constricting.”

“Well, there goes your brand deal.”

“Funny you should say, I’ve been scouting for new endorsers…” Cas leans in close enough to just brush his stone-hard length against Dean’s. Dean shudders. “Would you be interested?”

“Oh _hell yes.”_

Cas’s tongue swirls around the shell of his ear and Dean’s about to imagine all the other wonderful things that tongue could rim when Cas pulls back again to shimmying out of his pants. It’s a slow, strenuous tease that only picks up speed at the tip of Dean’s cock.  

Dean’s in the middle of fumbling with his belt when Cas’s hand wraps around the buckle. Cas’s hand over his alone is electrifying, but the new sight before him has his jaw mopping the floor with his drool: Cas’s cock is beautiful. It’s big without even straining to be, standing apart from his lean abdomen, and his balls are like two perfectly scooped strawberry sherbets.

Dean wants to extract as much cream as he can.

“Go ahead,” Cas states, again, reading his thoughts, and tugging him close again to brush his now bare dick against Dean’s still-clothed one. Dean actually whimpers this time, especially when a little more cum from Cas’s gorgeous prick smears his already stained tuxedo: It’s so hot, but so wrong. And there’s only one way to even out the damage.

Dean’s knees hit the tile with a _thud_.

Cas feels _amazing._ He traces every crease, memorizes every vein. He even extinguishes his precum with the pad of his tongue. But there’s so much of him. And so little time: It’s like wanting to get to the tootsie center. But judging by Cas’s hands burying in his hair and thrusting up and into him to fuck Dean’s face, Cas doesn’t mind him using a little teeth to get there.

Dean’s not sure what gets him off more: The guttural groan Cas makes when he shoots his load, or the action itself, so public and in so filthy a place, but it happens relatively quick.

“Ooh, Jesus Christ,” Dean sighs, eyes screwed shut. He’s not sure how long he’s standing there, catching his breath. He just knows it’s long enough for Cas to pulls his pants back up. When he finally opens his eyes, he makes his second mistake of the night of glancing down at his ensemble. “Ugh, Sam’s gonna have the upper hand on me for _years.”_

“I can clean you up,” Cas offers.

Dean shoots a second glance at the dispenser. “There’s no toilet paper.”

“I don’t need toilet paper.”

Dean fights against the new twitch in his crotch before holding up a finger. “No, no, I’m… I’m good.”

“At least let me clean your mouth.”

Dean shrugs. He can’t argue with that if he tried. Not only is he fucking tired, but Cas is still fucking gorgeous.

Cas leans in, hand resting over Dean’s hip. Only, instead of hosing Dean’s mouth off like a sprayer at a car wash, Cas quietly laps his tongue against his. Dean smiles against the kiss before they pull away.

 

 

Sure enough, Sam (and poor Jess) notices and gives him hell the rest of the week.

But when Dean empties his slacks for the washer that night and finds Cas’s number scribbled on a thin piece of toilet paper, he can’t help but look forward to being given the exact opposite very soon.


End file.
